Back in August, they went on a violent crime spree, and were finally caught after a 100 mph car chase in Colorado!

Now, we've learned that gangmember/sibling Dylan tried (and failed) to break out of jail, as described in a newly released prison document.

According to the doc, deputies found "a homemade knife and letter to the FBI in his cell." The letter read as follows:

"I have enjoyed staying here, so don't take any of this personal."

Ha! Apparently, the deputies also noticed that plumbing access had been "tampered with" in Dylan's cell, and that he had written another letter to his sister, which outlined his plan to "subdue the guards, steal their keys and escape with her."

Lee Grace goes on trial on Feb. 21 for attempted second-degree murder, assault, and other charges. Prosecutors in Florida are still deciding how to proceed with her brothers…although Dylan will face new counts of conspiracy to escape and possession of contraband for the escape plan.

Let's hope the Doughertys are able to stay out of trouble at least until their trials! Ugh.

P.S CLICK HERE to read up about the criminal spree of The Dougherty Gang AND to view some totally NSFW, nekkid pics of outlaw Lee Grace Dougherty!

Shane Redway -- a Canadian rapper and close friend of Drake's -- was killed early Saturday morning in a car crash. He was just 26 years old.

Redway and two others were killed when their car lost control, struck a guardrail and burst into flames. The crash occurred around 4am outside Pearson International Airport in Toronto. It's unclear who was behind the wheel. Police are investigating the crash.

Drake took to Instagram to remember Redway, posting two different tributes.